HCID 22064664, compound → HCID 22064712, compound

HRID 1828110Notes

Reaction equation

HRID 1828110 reaction equation
[C:1]([C:3]1[CH:28]=[CH:27][C:6]([CH2:7][NH:8][C:9](=[O:26])[CH:10]([O:23][CH2:24][CH3:25])[N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[F:21])[C:12]2=[O:22])=[C:5]([N+:29]([O-])=O)[CH:4]=1)#[N:2]>C(OCC)(=O)C.[Pd]>[NH2:29][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:28]=[CH:27][C:6]=1[CH2:7][NH:8][C:9](=[O:26])[CH:10]([O:23][CH2:24][CH3:25])[N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[F:21])[C:12]1=[O:22]

Participants

4

Reactant 1

HCID 22064664HCID 22064664, compound

Product 1

HCID 22064712HCID 22064712, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (RS)-N-(4-cyano-2-nitro-benzyl)-2-ethoxy-2-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide (0.310 g) in ethyl acetate (7.3 ml) was added 10% Pd/C (60 mg) and the mixture vigorously stirred at r.t. under a hydrogen atmosphere for 24 h. The catalyst was filtered off over a celite pad and the cake was carefully washed with ethyl acetate. The filtrate was evaporated to yield (RS)-N-(2-amino-4-cyano-benzyl)-2-ethoxy-2-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide (0.293 g) as yellow viscous oil, MS 397.2 ([M+H]+).

Workup

  1. filtrationThe catalyst was filtered off over a celite pad
  2. washthe cake was carefully washed with ethyl acetate
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-d57596b1165840f68b7d84b8993025f6
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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